Jeans always look trendy and chic with spiky heels.
If you like the look of heels but feel that it is not just you, go for wedge heels. Ranging from casual to chic, wedges come in all styles and heights. For a casual city look, opt for bright shades. But make sure you can carry the look.
Footwear with skirts basically depend on the length and style. You can choose from mere flip flops to classic pumps. While wearing knee high boots, assure that the length of the skirt and the length of the boot meet.
Stilettos look great with calf length and full length skirts. You can mix and match them with evening gowns, cocktails dresses or prom dresses. Stilettos makes a woman's leg appear hotter than any other type of shoes.
A fact : Did you know that the word 'Stiletto' is derived from an Italian word for dagger? It's sure there to kill :)
Finally learn to express your own personal style and still be hip.